AS Roma Vs AC Milan Timeline: Head-to-Head Record & Key Stats

Few fixtures in Italian football carry the weight of AS Roma vs AC Milan. It is a meeting of two different worlds: the capital’s burning passion and constant quest for validation against the structured, golden legacy of the industrial north. The rivalry between the Giallorossi and the Rossoneri is not just an ordinary fixture.

This is a tactical showdown, a spectacle of world-class talent, and a recurring narrative that has shaped Italian football across nearly a century. From Scudetto-deciding afternoons at the Stadio Olimpico to electric European nights at the San Siro, this timeline covers the moments that have defined one of Serie A’s most enduring sagas.

AS Roma Vs AC Milan Timeline & History

This is the complete AS Roma vs AC Milan timeline, covering every meeting between the two clubs from 1929 to 2026.

Across all competitions since their first meeting in 1929, AS Roma and AC Milan have produced one of Italian football’s most historically significant rivalries.

1989: Milan’s Era of Dominance

As the 1980s drew to a close, AC Milan under Arrigo Sacchi had become a global force. Their meeting with Roma in June 1989, played after the Scudetto had already been decided, served as a demonstration of the gulf in class between the league’s dominant side and its challengers.

That legendary Milan squad, built around Baresi, Maldini, and Van Basten, set the standard for what Italian football could look like at its most technically refined.

1998: The Rollercoaster at the San Siro

On October 25, 1998, a classic encounter between the two sides produced one of the more memorable scorelines in this fixture’s history. Roma, managed by Zdeněk Zeman, took the lead through Marco Delvecchio, but the match was chaotic throughout, with the lead changing hands before Milan secured a 3-2 victory.

George Weah was among the standout performers for Milan in a match that captured the unpredictability and tactical edge that made Serie A the most compelling league in the world during that era.

2004: The Scudetto Decider

Perhaps the most consequential single match in this rivalry’s modern history came on May 2, 2004. With the Scudetto on the line at the San Siro, Milan hosted second-placed Roma in a winner-takes-all atmosphere.

Andriy Shevchenko settled the contest early with a header, and that goal proved enough to secure Milan their 17th Serie A title, leaving Roma to reflect on a season in which they had pushed the champions to the very final day.

2006: Roma End Two Decades of San Siro Hurt

The 2006 season produced one of Roma’s most celebrated results in this fixture. Francesco Totti scored twice as Roma won 2-1 at the San Siro, ending a two-decade-long winless run for the Giallorossi at Milan’s home ground. The result remains one of the landmark moments in the rivalry’s recent history, confirming Roma’s growing ability to challenge Milan’s northern dominance on their own turf.

2009: A Farewell Spoiled

Roma delivered one of the more emotionally resonant results of the modern era in 2009, winning 3-2 at the San Siro in what proved to be Paolo Maldini’s farewell game for the club. For Milan supporters, the defeat stung doubly and not only a loss in a fixture of this magnitude, but a final memory of their iconic captain ending on the wrong side of a scoreline.

2012: The Ibrahimovic Masterclass

On March 24, 2012, Zlatan Ibrahimović produced a performance that encapsulated why he remains the leading goalscorer in the history of this fixture with 7 goals.

After falling behind to an Osvaldo strike, Milan rallied through the Swedish striker, who converted a penalty before finishing the game with a sublime chipped goal to clinch a 2-1 victory. It remains one of the most cited examples of individual brilliance defining the outcome of this rivalry.

2024: Roma’s Biggest Win and European Triumph

The 2024 calendar year delivered two landmark results for Roma. In Serie A, Roma produced their biggest ever win in this fixture, a stunning 5-2 victory over Milan. Months later, in the Europa League Quarter-Finals, Roma knocked Milan out of European competition with a 3-1 aggregate win across two legs (1-0 at the San Siro, 2-1 at the Stadio Olimpico), confirming that the balance of power between these two sides has shifted considerably in Roma’s favor in the current era.

2025: Milan’s San Siro Response

Milan’s biggest recent result came in 2025, a 3-1 home win that represented their most decisive margin of victory over Roma in the modern era. The result was a reminder that despite Roma’s recent resurgence, Milan’s home form at the San Siro remains a genuine advantage in this fixture.

January 25, 2026: The Latest Chapter

The most recent meeting between the two sides took place at the Stadio Olimpico on January 25, 2026, ending in a 1-1 draw. Milan drew first blood through Koni De Winter in the 62nd minute, converting from Luka Modrić’s precise cross, before Lorenzo Pellegrini equalized from the penalty spot in the 74th minute after a handball by Davide Bartesaghi.

Roma dominated in terms of chances, registering 15 shots to Milan’s 5 and an xG of 2.75 versus just 0.44 for the visitors, yet had to settle for a point. The result marked the 200th Serie A appearance for Milan defender Fikayo Tomori.

Head-to-Head Records

The all-time figures favor Milan decisively, reflecting their sustained dominance across the early and middle eras of Italian football. However, the modern era record tells a different story: since 2004, just two wins separate the sides across 53 matches, making this one of Serie A’s most genuinely competitive head-to-head fixtures in the current era.

Biggest wins:

• Roma’s biggest win in the fixture: 5-2 (2024)
• Milan’s biggest win in the fixture: 3-1 (2025, and again in 2024)

Recent Match: AS Roma Vs AC Milan

The most recent encounter between AS Roma vs AC Milan took place at the Stadio Olimpico, which concluded in a 1–1 draw, a result that reflected both Roma’s aggressive tactical approach and Milan’s resilience.

Recent Match Lineup: January 25, 2026

AS Roma Lineup (3-4-2-1)

• GK: Mile Svilar
• CB: Gianluca Mancini
• CB: Evan N’Dicka
• CB: Daniele Ghilardi
• RM: Mehmet Zeki Çelik
• CM: Bryan Cristante
• CM: Manu Koné
• LM: Wesley
• AM: Paulo Dybala
• AM: Matías Soulé
• CF: Donyell Malen

Substitutes: Lorenzo Pellegrini, Pierluigi Gollini, Devis Vásquez, Konstantinos Tsimikas, Jacek Ziółkowski, Naïm El Aynaoui, Lewis Ferguson, Niccolò Pisilli, Rodrigo Vaz, Leonardo Venturino, Edoardo Lulli.

Coach: Gian Piero Gasperini

AC Milan Lineup (3-5-2)

• GK: Mike Maignan
• CB: Fikayo Tomori
• CB: Matteo Gabbia
• CB: Koni De Winter
• RWB: Alexis Saelemaekers
• CM: Samuele Ricci
• CM: Luka Modrić
• CM: Adrien Rabiot
• LWB: Davide Bartesaghi
• CF: Christopher Nkunku
• CF: Rafael Leão

Substitutes: Filippo Terracciano, Noah Torriani, Zachary Athekame, Pervis Estupiñán, Daniel Odogu, Strahinja Pavlović, Youssouf Fofana, Ardon Jashari, Ruben Loftus-Cheek, Niclas Füllkrug, Christian Pulisic.

Coach: Massimiliano Allegri.

​Match Breakdown: AS Roma 1-1 AC Milan (January 25, 2026)

First Half

Roma started aggressively, forcing Mike Maignan into several crucial saves in the opening exchanges. Donyell Malen had the first effort on goal within 18 seconds of kickoff, making his home debut for the club. Despite Roma’s dominance in possession and territory, Maignan produced a stunning instinctive save from close range to deny Zeki Çelik in the 46th minute, ensuring the sides went in level at the break.

Second Half

62nd minute: Milan took the lead against the run of play. Luka Modrić whipped a precise short-corner delivery into the box, and Koni De Winter rose above the defense to power a header past Mile Svilar and now 1-0 to Milan.

74th minute: Roma restored parity from the spot. A cross from Çelik struck the arm of Davide Bartesaghi inside the box. Substitute Lorenzo Pellegrini stepped up and sent Maignan the wrong way making it 1-1.

Closing stages: Milan’s Niclas Füllkrug headed an Adrien Rabiot cross just over the bar in stoppage time, but neither side could find a winner.

Key Match Stats:

Shots: Roma 15, Milan 5

xG: Roma 2.75, Milan 0.44

Notable: Fikayo Tomori’s 200th appearance for AC Milan

Key Players in Rivalry

The rivalry between AS Roma vs AC Milan has been shaped by titans of the game whose technical brilliance, leadership, and defining moments in confrontations have written the history of this classic Serie A fixture.

Francesco Totti (AS Roma): The undisputed heart of the Giallorossi, Totti is the most significant figure in the history of this rivalry. His loyalty to Roma defined his 25-season career, and he stands as the highest scorer in head-to-head matches between these two clubs, having netted 11 goals against Milan.

For Totti, Milan was a consistent benchmark of excellence, and his performances against them often served as the true test of his and his team’s ambition.

​Paolo Maldini (AC Milan): If Totti was the passion and attacking spirit of the rivalry, Maldini was its calm, impenetrable foundation. As the defensive anchor for Milan, he faced Totti more than 30 times.

Their encounters were a masterclass in Italian football, thanks to the relentless, creative ingenuity of a legendary captain against the tactical intelligence and composure of one of the greatest defenders in history.

​Gunnar Nordahl (AC Milan/AS Roma): A unique figure in this saga, Nordahl holds the rare distinction of having scored for both clubs in their direct meetings.

His impact in the mid-20th century helped establish the rivalry’s competitive intensity, bridging the two institutions through his prolific goal-scoring.

Cafu (Roma/AC Milan): The legendary Brazilian wing-back was a vital part of Roma’s 2000/01 Scudetto-winning side before moving to Milan, where he became a cornerstone of their European-conquering teams.

​Stephan El Shaarawy (AC Milan/Roma): Having spent significant years at both clubs, El Shaarawy remains a bridge between the two modern eras, contributing speed and tactical versatility to both the Rossoneri and the Giallorossi attack.

​Christian Panucci (AC Milan/Roma): A stalwart in defense, Panucci enjoyed long spells at both clubs, bringing his elite experience and defensive solidity to the heart of the rivalry for over a decade.

Combined XI: Legends of Roma and Milan (4-3-1-2)

To honor the rich history between AS Roma vs AC Milan, we have curated a Combined XI featuring the most iconic legends who have graced this rivalry.

The lineup balances the defensive steel of the Rossoneri with the creative, passionate heart of the Giallorossi.

The Combined XI: Legends of Roma & Milan (4-3-1-2)

GK: Gianluigi Buffon

RB: Cafu

CB: Franco Baresi

CB: Aldair

LB: Paolo Maldini

DM: Daniele De Rossi

CM: Andrea Pirlo

AM: Kaká

AM: Francesco Totti

CF: Gabriel Batistuta

CF: Marco van Basten